반응 #1132544

반응 방정식

3-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde

methyl iodide

cesium carbonate

→

4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde

수율 85.3%

용매

dimethylformamide

반응 조건

후처리

1. 1
   기타The reaction mixture was irradiated by microwave at 100° C. for 30 minutes
2. 2
   기타The solvent was removed
3. 3
   세척the residue was washed with water
4. 4
   추출extracted with dichloromethane
5. 5
   기타Purification by silica chromatography (ISCO)

실험 절차

3-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde (0.5 g, 2.82 mmol), methyl iodide (0.6 g, 4.23 mmol) and cesium carbonate (1.37 g, 4.23 mmol) were dissolved in dry dimethylformamide (2 mL). The reaction mixture was irradiated by microwave at 100° C. for 30 minutes. The solvent was removed and the residue was washed with water and extracted with dichloromethane. Purification by silica chromatography (ISCO) produced 4-methyl-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbaldehyde (0.46 g, 85%). 1H NMR (400 MHz, DMSO-d6): δ 9.95 (s, 1H), 7.62 (s, 1H), 7.59 (d, 1H), 7.20 (d, 1H), 4.80 (s, 2H), 3.34 (s, 3H); MS (ESI) m/z: Calculated for C10H9NO3: 191.1. found: 192.1 (M+H)+.

출처